Enantio- and Diastereoselective Cross-annulation of Enal and Ketone with New Chiral Bicyclic <i>N</i>-Heterocyclic Carbene Catalysts

• Hasegawa Momo

  Department of Chemistry, Graduate School of Science, Chiba University

• Yoshida Kazuhiro

  Department of Chemistry, Graduate School of Science, Chiba University Molecular Chirality Research Center, Chiba University

• Yanagisawa Akira

  Department of Chemistry, Graduate School of Science, Chiba University Molecular Chirality Research Center, Chiba University

Abstract

The enantio- and diastereoselective cross-annulation of cinnamaldehyde (6) and 2,2,2-trifluoroacetophenone (7) was examined to evaluate the performance of newly developed chiral bicyclic imidazolium salts 3 and 4 as catalyst precursors. The reaction proceeded to give desired γ-lactone 8 with high diastereoselectivities (up to 10/1) and moderate enantioselectivities (up to 71% ee) when the sterically demanding catalyst precursors were used.

Journal

• Chemistry Letters

  Chemistry Letters 45 (3), 294-296, 2016

  The Chemical Society of Japan

Keywords

• <i>N</i>-Heterocyclic carbene (NHC)
• Cross-annulation
• Chiral bicyclic NHC catalyst

Details

• CRID: 1390001204587972352
• NII Article ID: 130005132185
• DOI: 10.1246/cl.151116
• ISSN: 13480715
• ISSN: 03667022
• Web Site: http://www.journal.csj.jp/doi/pdf/10.1246/cl.151116
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed